Hydroformylation By Reacting Ethylenically Unsaturated Compound, Carbon Monoxide And Gaseous Hydrogen Patents (Class 568/429)
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Patent number: 6579997Abstract: A metallacrown ether ligand chelates a transition metal atom to form a catalyst well suited to perform hydroformylation in the presence of carbon monoxide, hydrogen and an unsaturated substrate compound.Type: GrantFiled: July 3, 2002Date of Patent: June 17, 2003Assignee: UAB Research FoundationInventors: Gary M. Gray, Maheswaran Harihara Sarma, Dale C. Smith
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Patent number: 6559344Abstract: In a process for the hydroformylation of ethylenically unsaturated compounds, at least one complex or compound of a metal of transition group VIII with at least one bidentate phosphine ligand is used as hydroformylation catalyst and at least one of the reaction steps following the hydroformylation reaction is carried out essentially in the absence of carbon monoxide and hydrogen and in the presence of at least one monodentate phosphine ligand.Type: GrantFiled: February 19, 2002Date of Patent: May 6, 2003Assignee: BASF AktiengesellschaftInventor: Thomas Mackewitz
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Publication number: 20020198403Abstract: The subject for the invention is to efficiently use, recover, and reuse a soluble metallic catalyst with great ease at low cost in various liquid-phase reactions using the soluble metallic catalyst.Type: ApplicationFiled: March 25, 2002Publication date: December 26, 2002Applicant: NIPPON SHOKUBAI CO., LTD.Inventor: Takafumi Kubo
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Patent number: 6492525Abstract: The invention concerns novel organometallic complexes comprising cationic heterocyclic carbenes. It also concerns a method for preparing said complexes from dicationic heterocyclic precursor compounds. It further concerns the use as catalysts of said organometallic complexes for a certain number of chemical reactions.Type: GrantFiled: June 21, 2001Date of Patent: December 10, 2002Assignee: Rhodia Fiber & Resin IntermediatesInventors: Guy Bertrand, Lutz Stelzig, Olivier Guerret, Christophe Buron, Heinz Gornitzka, Paolo Burattin
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Publication number: 20020161266Abstract: The present invention is drawn to a method of performing a one-pot organic reactions including carbon monoxide as reactant, without the use of an external CO gas source, wherein a reaction mixture containing a solid or liquid CO releasing compound, a non-metal substrate and a metal catalyst is exposed to an energy source to release carbon monoxide from the CO releasing compound and wherein carbon atoms of the released carbon monoxide form a bond with the non-metal substrate compound. The present invention is further drawn to a method of preparing chemical libraries and a kit for organic reactions.Type: ApplicationFiled: December 14, 2001Publication date: October 31, 2002Inventors: Mats Larhed, Mathias Alterman, Yiqian Wan, Anders Hallberg, Nils-Fredrik Kaiser
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Patent number: 6403836Abstract: The present invention is a process for preparing C4-25 aldehydes by hydroformylating the corresponding C3-24 olefins in the presence of a cobalt hydroformylation catalyst, and catalytically decomposing the formic acid formed in the hydroformylation reaction or in the subsequent catalyst work-up. The aldehydes so produced may be hydrogenated to form alcohols.Type: GrantFiled: February 22, 2001Date of Patent: June 11, 2002Assignee: Oxeno Olefinchemie GmbHInventors: Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Felix Gosmann
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Patent number: 6388141Abstract: The present invention relates to processes for the preparation of oxo products by the hydroformylation of substrates having C═C double bonds using unmodified rhodium catalysts in a reaction mixture essentially consisting of the substrates, the catalyst and carbon dioxide in a supercritical state (scCO2). In particular, the invention relates to such processes for the preparation of products which contain substantial proportions of branched i-oxo products. Further, the invention relates to such processes for the hydroformylation of substrates which do not correspond to the general formula CnH2n. The invention further relates to such processes in which the separation of product and catalyst is effected using the special solvent properties of scCO2.Type: GrantFiled: January 13, 2000Date of Patent: May 14, 2002Assignee: Studiengesellschaft Kohle mbHInventors: Walter Leitner, Daniel Koch
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Publication number: 20020042541Abstract: The invention relates to a process for producing a bis(trifluoromethyl)benzaldehyde represented by the general formula [1].Type: ApplicationFiled: June 26, 2001Publication date: April 11, 2002Inventor: Takeo Komata
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Patent number: 6369257Abstract: Supported bis(phosphorus) ligands are disclosed for use in hydroformylation reactions, including the hydroformylation of olefins. Catalysts are formed when the ligands are complexed with a catalytically active metal (e.g., rhodium or iridium).Type: GrantFiled: February 16, 2001Date of Patent: April 9, 2002Assignee: E. I. du Pont de Nemours and CompanyInventors: Emilio E. Bunel, Patrick Michael Burke, Joe Douglas Druliner, Leo Ernest Manzer, Kenneth Gene Moloy, Manxue Wang
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Patent number: 6362305Abstract: In a process for preparing formaldehyde from methanol by dehydrogenation in a reactor in the presence of a catalyst at a temperature in the range from 300 to 1000° C., a circulating gas stream comprising by-products of the dehydrogenation is passed through the reactor.Type: GrantFiled: February 28, 2000Date of Patent: March 26, 2002Assignee: Ticona GmbHInventors: Elke Schweers, Thomas Kaiser, Christine Meister, Michael Rosenberg, Rolf Schulz
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Publication number: 20020028974Abstract: Olefins are hydroformylated to give alcohols and/or aldehydes in a plurality of hydroformylation stages, each of which comprises:Type: ApplicationFiled: July 16, 2001Publication date: March 7, 2002Applicant: OXENO Olefinchemie GmbHInventors: Bernhard Scholz, Franz Nierlich, Alfred Kaizik, Dieter Hess, Wilfried Bueschken, Klaus-Diether Wiese, Dirk Roettger, Guido Protzmann
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Patent number: 6229052Abstract: Supported bis(phosphorus) ligands are disclosed for use in hydroformylation reactions, including the hydroformylation of olefins. Catalysts are formed when the ligands are complexed with a catalytically active metal (e.g., rhodium or iridium).Type: GrantFiled: April 14, 1999Date of Patent: May 8, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Emilio E. Bunel, Patrick Michael Burke, Joe Douglas Druliner, Leo Ernest Manzer, Kenneth Gene Moloy, Manxue Wang
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Patent number: 5910600Abstract: A bisphosphite compound of the following formula (A): ##STR1## wherein --Ar--Ar-- is a bisarylene group represented by any one of the formulae (A-I) to (A-III) defined in the specification, and each of Z.sub.1 to Z.sub.4 is a C.sub.4-20 aromatic or heteroaromatic group which may have a substituent, wherein each of substituents on carbon atoms of an aromatic ring adjacent to the carbon atom bonded to the oxygen atom in each of Z.sub.1 to Z.sub.4, is a C.sub.0-2 group, and each pair of Z.sub.1 and Z.sub.2, and Z.sub.3 and Z.sub.4, are not bonded to each other.Type: GrantFiled: April 28, 1997Date of Patent: June 8, 1999Assignee: Mitsubishi Chemical CorporationInventors: Hisao Urata, Hiroaki Itagaki, Eitaro Takahashi, Yasuhiro Wada, Yoshiyuki Tanaka, Yasukazu Ogino
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Patent number: 5817850Abstract: The synthesis of new sterically hindered ferrocene bis(phosphonites) of formula I ##STR1## the synthesis of the corresponding transition-metal complexes and the use of these complexes in transition-metal-catalyzed reactions are described.Type: GrantFiled: October 30, 1997Date of Patent: October 6, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Stephen D. Pastor, Sai P. Shum
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Patent number: 5498801Abstract: A process is effected using water soluble metal complex catalysts in the presence of a promoter in the organic (water immiscible) phase. The process results in the enhancement of the rate of hydroformylation by interfacial catalysis induced by the presence of a ligand (promoter) in a catalyst immiscible phase. The reaction comprises of two phases viz - organic phase and aqueous phase. The organic phase consists of an olefin and P- containing water insoluble ligand with or without water immiscible solvent. The aqueous phase consists of a metal complex catalyst comprising of group VIII element such as Rh, Ru, Ir or Co and a water soluble ligand.Type: GrantFiled: December 30, 1994Date of Patent: March 12, 1996Assignee: Council of Scientific & Industrial InterestInventors: Raghunath V. Chaudhari, Bhalchandra M. Bhanage, Sunil S. Divekar, Raj M. Deshpande
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Patent number: 5488174Abstract: Process for the hydroformylation of ethylenically unsaturated compounds, by reaction with carbon monoxide and hydrogen in the presence of a catalyst based on a metal of the platinum group, a source of anions and a bidentate ligand of the formula R.sup.1 R.sup.2 M.sup.1 RM.sup.2 R.sup.3 R.sup.4 wherein M.sup.1 and M.sup.2 are phosphorus, arsenic or antimony, R is a bivalent organic bridging group with 1 to 4 atoms in the bridge, R.sup.1 and R.sup.2 together represent a bivalent cyclic group and R.sup.3 and R.sup.4 independently represent an optionally substituted hydrocarbyl group or together have the same meaning as R.sup.1 and R.sup.2.Type: GrantFiled: August 12, 1994Date of Patent: January 30, 1996Assignee: Shell Oil CompanyInventors: Eit Drent, Dennis H. L. Pello, Jacoba C. L. J. Suykerbuyk
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Patent number: 5481044Abstract: .alpha.-alkyl aldehydes having 8 to 17 carbon atoms are obtained from terminal olefins containing one less carbon atom. The olefins are first isomerized in the presence of iron carbonyl and then, without separating out the iron compound, hydroformylated in the presence of rhodium as catalyst.Type: GrantFiled: December 15, 1994Date of Patent: January 2, 1996Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Helmut Springer
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Patent number: 5475146Abstract: Enantioselective hydroformylation of vinyl compounds using a catalyst composition of a chiral carbohydrate phosphorous ligand with a Rh, Pt, Co or Ir metal, to produce chiral 2-substituted propanals, wherein the phosphorous of the ligand is substituted with electron withdrawing groups.Type: GrantFiled: September 2, 1993Date of Patent: December 12, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Timothy A. Ayers, Thaliyil V. Rajanbabu
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Patent number: 5463082Abstract: Stoichiometric and catalytic chemical transformations may be carried out in solution using novel fluorous multiphase systems (FMS). The term "fluorous" is defined as a carbon-fluorine bond rich organic molecule. The FMS consists of a fluorous phase containing a fluorous solvent, typically a fluorocarbon or a fluorohydrocarbon and a reagent or a catalyst containing a sufficient number of fluorous moieties to render it preferentially soluble in the fluorous solvent without impairing the ability of the catalyst or reagent to be effective in the reaction and while maintaining the reaction in a liquid or fluid phase. The nonfluorous solvent may be any suitable organic or nonorganic solvent(s) with limited or no solubility in the fluorous solvent that is effective for dissolving the reactant(s) and most desirably, for separating the resulting product(s). Typically, such solvents have a Hildebrand solubility parameter of at least about 18.0 MPa1/2.Type: GrantFiled: July 8, 1993Date of Patent: October 31, 1995Assignee: Exxon Research and Engineering CompanyInventors: Istvan T. Horvath, Jozsef Rabai
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Patent number: 5463137Abstract: A propylene stream which contains propane as an impurity is contacted with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst thereby producing a product stream containing butyraldehyde and/or n-butyl alcohol, unreacted propylene and propane. A gas mixture containing propylene and propane is separated from the product stream and subjected to adsorption at a temperature of 0.degree. to 250.degree. C. in a bed of adsorbent which selectively adsorbs propylene, thereby adsorbing substantially all of the propylene from the gas mixture. The propylene is desorbed from the adsorbent and recycled to the reaction zone. The process is operated on a low per pass conversion with recycle of unreacted propylene. In the system of the invention the propylene adsorption unit may be upstream or downstream of the hydroformylation reactor.Type: GrantFiled: April 22, 1994Date of Patent: October 31, 1995Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Loc H. Dao
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Patent number: 5436374Abstract: A process for producing a 4-formyl-4'-methylbiphenyl from a biphenyl which comprises conducting the carbonylation of the biphenyl with carbon monoxide in the presence of a HF-BF.sub.3 catalyst in a carbonylation reactor to obtain the resulting reaction product solution containing a 4-formylbiphenyl, separating the 4-formylbiphenyl from the reaction product solution, hydrogenating the separated 4-formylbiphenyl to obtain a 4-methylbiphenyl, recycling the 4-methylbiphenyl to the carbonylation reactor, and then conducting both the carbonylation of the biphenyl with carbon monoxide to obtain a formylbiphenyl and the carbonylation of the 4-methylbiphenyl with carbon monoxide to obtain a 4-formyl-4'-methylbiphenyl simultaneously in the presence of the HF-BF.sub.3 catalyst in the carbonylation reactor.Type: GrantFiled: July 28, 1994Date of Patent: July 25, 1995Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Makoto Komatsu, Susumu Fujiyama, Koichi Kida, Mitsuharu Kitamura
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Patent number: 5430194Abstract: The present invention relates to a process for producing an optically active aldehyde (first aldehyde) containing a reduced amount of the corresponding enantiomeric aldehyde (second aldehyde) which process comprises: (1) providing an initial solution containing a non-eutectic mixture of the first aldehyde and the second aldehyde, which mixture has a composition in the compositional region where only the first aldehyde crystallizes when its solubility limit in the solution is exceeded, and (2) maintaining the solution at a temperature above the eutectic temperature of the mixture and under conditions such that the solubility limit of the first aldehyde is exceeded so as to form a crystalline first aldehyde containing relatively less of the second aldehyde than was present in the initial solution.Type: GrantFiled: June 24, 1994Date of Patent: July 4, 1995Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Bruce A. Barner, John R. Briggs, Jonathan J. Kurland, Charles G. Moyers, Jr.
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Patent number: 5382701Abstract: A method for producing a potassium paradiphenyl phosphino sulfonate ligand which comprises reacting potassium diphenyl phosphide with a lithium salt of para-chloro benzenesulfonic acid in the presence of tetrahydrofuran at elevated temperatures.Type: GrantFiled: November 18, 1993Date of Patent: January 17, 1995Assignee: Exxon Chemical Patents Inc.Inventors: Elena N. Suciu, Joel R. Livingston, Jr., Edmund J. Mozeleski
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Patent number: 5364950Abstract: This invention provides a process for stabilizing a phosphite ligand against degradation in a homogeneous reaction mixture containing a Group VIII transition metal catalyst and the phosphite ligand, said process comprising adding to the reaction mixture an epoxide in an amount from 0.001 to 5 weight percent based on the total weight of the reaction mixture to reduce the degradation of the ligand.Type: GrantFiled: September 29, 1992Date of Patent: November 15, 1994Assignee: Union Carbide Chimicals & Plastics Technology CorporationInventors: James E. Babin, John M. Maher, Ernst Billig
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Patent number: 5260477Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises a step (I) of dehydrogenating p-isobutylethylbenzene in a gaseous phase in the presence of a dehydrogenating metal catalyst to form p-isobutylstyrene and at least one unsaturated hydrocarbon compound selected from a group A defined in Claim 1; a step (II) of reacting p-isobutylstyrene obtained in the step (I) with carbon monoxide and hydrogen or with carbon monoxide and water or a lower alcohol in the presence of a transition metal complex carbonylating catalyst to form .alpha.-(4-isobutylphenyl)propionic acid or its precursor; and a step (III) of hydrogenating at least one unsaturated hydrocarbon compound selected from the group A obtained in the dehydrogenation step (I) to form p-isobutylethylbenzene, and recycling the thus formed p-isobutylethylbenzene through the step (I) as the raw material of the step (I).Type: GrantFiled: December 18, 1989Date of Patent: November 9, 1993Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Yuichi Tokumoto, Kazumichi Uchida
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Patent number: 5223648Abstract: The hydroformylation of olefins and olefinically unsaturated compounds in the presence of a water-soluble rhodium complex compound Which contains, as a ligand, at least one sulfonated diphosphine, and a catalyst therefor.Type: GrantFiled: August 25, 1992Date of Patent: June 29, 1993Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Herrmann, Christian Kohlpaintner, Helmut Bahrmann
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Patent number: 5191121Abstract: A novel aroyl ketone derivative represented by formula (I) is disclosed.Ar(COCH.sub.2 COR.sup.1).sub.n (I)wherein R.sup.1 represents a saturated or unsaturated hydrocarbon group having 1-24 carbon atoms, or a linear or branched alkoxyalkyl or alkenyloxyalkyl group having 1-24 carbon atoms, dialkylamino group having 1-24 carbon atoms, Ar represents a benzene or naphthalene ring which may be substituted with one or more hydroxyl groups, alkoxy groups having 1-24 carbon atoms, alkenyloxy groups having 1-24 carbon atoms, polyoxyleneoxy groups, mono- or dialkyl amino groups having 1-24 carbon atoms, or .alpha.-methylenedioxy groups, and n denotes an integer of 1-4. An UV-ray absorber and cosmetic composition comprising the aroyl ketone derivative of formula (I) are also disclosed.Type: GrantFiled: April 15, 1991Date of Patent: March 2, 1993Assignee: Kao CorporationInventors: Shinji Yamada, Akira Kawamata, Genji Imokawa, Shinichi Masuda, Masakazu Yamaguchi, Kouichi Niinaka, Hiroko Joukura
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Patent number: 5166419Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises the following steps (I), (II) and (III):step (I): subjecting isobutylbenzene and a polyalkylbenzene to disproportionation reaction in order to form p-isobutylethylbenzenestep (II): dehydrogenating p-isobutylethylbenzene obtained in the step (I) to form p-isobutylstyrene, andstep (III): the following step (IIIa) or (IIIb):step (IIIa): reacting p-isobutylstyrene obtained in the step (II) with carbon monoxide and hydrogen to prepare .alpha.-(4-isobutylphenyl)propionaldehyde, orstep (IIIb): reacting p-isobutylstyrene obtained in the preceding step (II) with carbon monoxide and water or a lower alcohol to prepare .alpha.-(4-isobutylphenyl)propionic acid or its alkyl ester.Type: GrantFiled: August 22, 1990Date of Patent: November 24, 1992Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Yuuichi Tokumoto, Isoo Shimizu, Satoru Inoue
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Patent number: 5118824Abstract: The invention relates to platinum hydrides, a process for their preparation and their use as components of catalytic systems. The platinum hydrides have a bridged bimetallic structure represented by the general formula: ##STR1## wherein: M is a metal of valence n, at least equal to 2,X is a halogen atom, andP P is a schematic representation of a ligand of the general formula: ##STR2## in which: R.sub.1, R.sub.2, R.sub.5, and R.sub.6, identical or different, are chosen from among aliphatic or cycloaliphatic hydrocarbon radicals with 1 to 8 carbon atoms and aromatic hydrocarbon radicals with 6 to 10 carbon atoms,R.sub.3 and R.sub.4, identical or different, are chosen from among a hydrogen atom and aliphatic hydrocarbon radicals with 1 to 8 carbon atoms, possibly functionalized and/or together forming a ring, andm is an integer higher than or equal to 4.Type: GrantFiled: February 6, 1991Date of Patent: June 2, 1992Assignee: AtochemInventors: Eric Paumard, Andre Mortreuz, Francis Petit
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Patent number: 5099047Abstract: A method for recovering a Group VIII metal solid complex from an organic compound-containing solution containing a Group VIII metal complex, wherein the Group VIII metal complex is precipitated in the presence of a trialkyl phosphine of the following formula (I): ##STR1## wherein each of R.sub.1, R.sub.2 and R.sub.3 is an alkyl group and they may be the same or different from one another, and the sum of the carbon numbers of R.sub.1, R.sub.2 and R.sub.3 is at least 42.Type: GrantFiled: November 13, 1990Date of Patent: March 24, 1992Assignee: Mitsubishi Kasei CorporationInventors: Keiichi Sato, Yuji Kawaragi
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Patent number: 5097061Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises a step A of forming p-isobutylstyrene from p-isobutylethylbenzene and a step B of forming .alpha.-(4-isobutylphenyl)propionaldehyde from p-isobutylstyrene or a step C of forming .alpha.-(4-isobutylphenyl)propionic acid or its alkyl ester from p-isobutylstyrene.Furthermore, a method for preparing said p-isobutylethylbenzene is also disclosed which comprises alkylating isobutylbenzene or 4-ethyltoluene with ethylene or propylene.Type: GrantFiled: June 19, 1989Date of Patent: March 17, 1992Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Yuuichi Tokumoto, Kazumichi Uchida
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Patent number: 5072037Abstract: A process for the preparation of 2-(4-chlorophenyl)-3-methylbutyric acid from 4-chlorobenzaldehyde by conversion of the benzaldehyde to 3-(4-chlorophenyl)-2-methylpropenal, 3-(4-chlorophenyl)-2-methylpropanol, 1-(4-chlorophenyl)-2-methylpropene-1, and 2-(4-chlorophenyl)-2-methylbutyraldehyde, and finally to the desired corresponding butyric acid.Type: GrantFiled: December 21, 1990Date of Patent: December 10, 1991Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Peter Lappe, Helmut Springer
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Patent number: 4999450Abstract: A process for preparing .alpha.-(3-benzylphenyl)-propionic acid or its derivative, a precursor of ketoprofen (trade name), which comprises dehydrogenating a by-product oil fraction formed in the production of ethylbenzene using synthetic zeolite as an alkylating catalyst, and carbonylating the product with carbon monoxide or the like. This precursor can be easily converted into ketoprofen, a useful medicine as an anti-inflammatory agent.Type: GrantFiled: March 23, 1990Date of Patent: March 12, 1991Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yasuo Matsumura, Yutaka Arai
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Patent number: 4982007Abstract: A process for selectively hydroformylating a diolefin, which comprises reacting a (1-arylethyl)vinylbenzene with carbon monoxide and hydrogen under the conditions of 40.degree. to 200.degree. C. in reaction temperature and 5 kg/cm.sup.2 or above in reaction pressure in the presence of a transition metal carbonylation catalyst to thereby selectively hydroformylating only the vinyl group and produce .alpha.-((1-arylethenyl)phenyl)propionaldehyde. The starting material to be hydroformylated may be a mixture of the (1-arylethenyl)vinylbenzene with a 1,1-di(substituted aryl)ethylene not substituted by a vinyl group.Type: GrantFiled: March 2, 1990Date of Patent: January 1, 1991Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yasuo Matsumura, Yutaka Arai
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Patent number: 4978801Abstract: Aromatic aldehydes are more efficiently produced by reacting carbon monoxide/hydrogen admixture with an aromatic halide in the presence of a noble metal-based catalyst, a tertiary nitrogenous based and, if necessary, a noble metal complexing agent, e.g., a phosphine or phosphite, wherein the CO/H.sub.2 ratio is less than 1.Type: GrantFiled: April 28, 1987Date of Patent: December 18, 1990Assignee: Rhone-Poulenc ChimieInventors: Norbert Bluthe, Robert Perron
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Patent number: 4973741Abstract: A process for producing a .beta.-hydroxyester product or a .beta.-hydroxyaldehyde product from ethylene oxide, carbon monoxide, and, optionally, hydrogen, is disclosed. This process uses, as a catalyst, a catalyst comprising rhodium, ruthenium, and a Group Va promoter.Type: GrantFiled: June 29, 1989Date of Patent: November 27, 1990Assignee: Eastman Kodak CompanyInventor: William A. Beavers
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Patent number: 4929767Abstract: A process for treating an organic solution of a partially deactivated solubilized rhodium-tertiary organophosphine complex hydroformylation catalyst with an organic reagent in order to improve the extractability of rhodium therefrom into an aqueous solution containing an ionic organophosphine ligand.Type: GrantFiled: October 6, 1988Date of Patent: May 29, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: David J. Miller, David R. Bryant, Ernst Billig, Bernard L. Shaw
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Patent number: 4782188Abstract: The invention is a process for the hydroformylation of C.sub.2-4 alkenes, formyl-substituted C.sub.2-4 alkenes, aryl-substituted alkenes, unsaturated norbornane ring-containing compounds, and .alpha.-unsaturated acetals which comprises contacting a C.sub.2-4 alkene, a formyl-substituted C.sub.2-4 alkene, aryl-substituted alkene, an unsaturated norbornane ring-containing compound or an .alpha.-unsaturated acetal in a polar organic solvent with water and carbon monoxide in the presence of a catalytic amount of a catalyst which comprises a mixture of (a) an alkali metal iron carbonyl or alkaline earth metal iron carbonyl which corresponds to the formula M.sub.a Fe.sub.x (CO).sub.y and (b) iron pentacarbonyl under conditions such that an alcohol or aldehyde derivative of a C.sub.2-4 alkene, a formyl-substituted C.sub.2-4 alkene, an aryl-substituted alkene, unsaturated norbornane ring-containing compound or an .alpha.Type: GrantFiled: November 14, 1983Date of Patent: November 1, 1988Assignee: The Dow Chemical CompanyInventor: Susan B. Butts
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Patent number: 4694100Abstract: A method for producing .alpha.-(p-isobutylphenyl)propionic acid or its alkyl esters which is characterized in that starting materials are inexpensive, processes are easy to be done and products are highly pure. The method comprises the steps of (I): catalytically cracking 1,1-bis(p-isobutylphenyl)ethane at temperatures in the range of 200.degree. to 650.degree. C. in the presence of a protonic acid catalyst and/or a solid acid catalyst to produce isobutylbenzene and p-isobutylstyrene; and (II): reacting said p-isobutylstyrene with carbon monoxide and water or alcohol at temperatures in the range of 40.degree. to 150.degree. C. in the presence of a metal complex carbonylation catalyst to produce .alpha.-(p-isobutylphenyl)propionic acid or its alkyl ester; or (III): reacting said p-isobutylstyrene with carbon monoxide and hydrogen at temperatures in the range of 40.degree. to 150.degree. C. in the presence of a metal complex carbonylation catalyst to produce .alpha.Type: GrantFiled: July 10, 1985Date of Patent: September 15, 1987Assignee: Nippon Petrochemicals Company, Ltd.Inventors: Isoo Shimizu, Ryotaro Hirano, Yasuo Matsumura, Hideki Nomura, Kazumichi Uchida, Atsushi Sato
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Patent number: 4613702Abstract: Aldehydes are facilely prepared in high yields by catalytically hydrocarbonylating an organic halide with gaseous admixture of hydrogen and carbon monoxide in the presence of a neutralizing agent for the hydrogen acid produced thereby, said hydrocarbonylation being carried out in an inert, liquid carboxylic acid reaction medium, i.e., a liquid carboxylic acid which is inert under the reaction conditions of temperature and pressure.Type: GrantFiled: May 15, 1985Date of Patent: September 23, 1986Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Philippe Leconte
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Patent number: 4585897Abstract: A process for hydration and condensation of acetylene in a crude acetylene stream containing water in the presence of a zirconia-alumina catalyst containing water to prepare aliphatic, aromatic and oxygenated compounds suitable for use as high octane liquid water fuels and as octane improvers for motor fuels is disclosed.Type: GrantFiled: August 24, 1984Date of Patent: April 29, 1986Assignee: Standard Oil Company (Indiana)Inventors: Ellis K. Fields, Mark L. Winzenburg, David A. De Marco
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Patent number: 4549015Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification.The new compounds are useful e.g. as stabilizers in photographic material.Type: GrantFiled: June 14, 1983Date of Patent: October 22, 1985Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4532364Abstract: Described are ether carboxaldehydes defined according to the generic structure: ##STR1## wherein X represents aryl, alkaryl, hydroxyalkyl, alkenyl, cycloalkenyl, lower alkyl or bicycloalkyl; wherein Y represents C.sub.1 -C.sub.3 lower alkylene; wherein Z completes an alkyl substituted C.sub.6 cycloalkyl ring or represents no moiety; wherein R represents hydrogen or methyl; wherein m represents 0 or 1; wherein n represents 0 or 1; wherein p represents 0 or 1 and wherein q represents 0 or 1 with the provisos that when m is 1, Z completes the alkyl substituted or unsubstituted C.sub.Type: GrantFiled: September 19, 1983Date of Patent: July 30, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4528404Abstract: Certain triarylphosphine rhodium carbonyl hydride complexes(Ar.sub.3 P).sub.3 Rh(CO)H (I) and (Ar.sub.3 P).sub.2 Rh(CO).sub.2 H (II)are selective and stable catalysts of high temperature olefin hydroformylation. The critical factors are the maintenance of a sufficient CO partial pressure, above 25 psia, and the provision of a high excess of triarylphosphine ligand concentration, at a minimum of 1 mole per kg. To provide a high ratio of n- to i-aldehyde products of 1-olefin hydroformylation, the concentration of the tris-phosphine complex (I) is maximized. In a continuous product flashoff operation of the present process, the major high boiling solvent components are the excess phosphine ligands and monoalcohol and monoester by-products.A combined isomerization-hydroformylation process is also disclosed for the selective conversion of internal linear olefins to terminal n-aldehydes. In this process, the concentration of the bis-phosphine complex (II) is minimized.Type: GrantFiled: October 23, 1984Date of Patent: July 9, 1985Assignee: Exxon Research and Engineering Co.Inventors: Alexis A. Oswald, Joseph S. Merola, John C. Reisch, Rodney V. Kastrup
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Patent number: 4521634Abstract: Described are ether carbinols defined according to the generic structure: ##STR1## wherein X.sub.1 represents a moiety selected from the group consisting of: ##STR2## and wherein Y.sub.1 represents C.sub.4 or C.sub.5 alkylene or C.sub.4 or C.sub.5 alkenylene or C.sub.4 or C.sub.5 alkynylene; processes for preparing such ether carbinols by means of first reacting allyl ethers with a mixture of carbon monoxide and hydrogen by means of an oxoreaction to produce ether carboxaldehydes and then reducing the thus formed ether carboxaldehydes to ether carbinols; or reacting camphene with appropriate diols; as well as methods for augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes and perfumed articles; foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes; and smoking tobaccos and smoking tobacco articles by adding thereto an aroma or taste augmenting or enhancing quantity of the thus produced ether carbinols.Type: GrantFiled: January 26, 1984Date of Patent: June 4, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4487972Abstract: This specification discloses a process for the production of oxygenated compounds, more specifically aldehydes and alcohols, by reacting an olefin with hydrogen and carbon monoxide in the presence of, as a ctalyst, an insoluble polymer containing a functional group, which may be an amine, thiol, phosphine, or arsine group, having chemically bonded thereto a metal of Group VIII of the Periodic Table. The metal can be, for example, rhodium, cobalt, or ruthenium. The olefin can contain more than one carbon-to-carbon double bond, may be an open chain or a cyclic olefin, and may be substituted. Further, the olefin may be contained in a refinery stream such as a cracked gasoline. The reaction may be carried out in the presence of a polar solvent.Type: GrantFiled: April 22, 1980Date of Patent: December 11, 1984Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Darrell D. Whitehurst
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Patent number: 4482748Abstract: The homogeneous catalysis of the hydrocarbonylation of olefins using a catalyst comprising a complex between an organic ligand and a Group VIII noble metal hydride carbonyl. The reaction is performed at mild conditions including temperatures from 50.degree.-200.degree. C. and pressures from 1 to 10,000 atmospheres to produce a predominantly aldehyde product having a high normal to iso distribution. The aldehyde products so produced are useful as intermediates for hydrogenation to aliphatic alcohols, for aldol condensation to produce plasticizers, for oxidation to produce aliphatic acids, etc.Type: GrantFiled: July 19, 1978Date of Patent: November 13, 1984Assignee: Celanese CorporationInventor: Frank B. Booth
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Patent number: 4435585Abstract: There is disclosed a novel process for preparing a number of cinnamaldehyde derivatives. These cinnamaldehyde derivatives can be reduced to dihydrocinnamaldehyde derivatives, a number of which are commercially important in the preparation of fragrances. The invention is also directed to a number of novel intermediates and their preparation.Type: GrantFiled: November 17, 1981Date of Patent: March 6, 1984Assignee: Givaudan CorporationInventors: Yvo Crameri, Paul A. Ochsner, Peter Schudel
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Patent number: 4334042Abstract: In the carbonylation of olefinic compounds in the presence of a cobalt carbonyl catalyst, the addition to the reaction system of a secondary phosphine oxide represented by the general formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each is substituted or unsubstituted hydrocarbon residue having not more than about 20 carbon atoms, in an amount of 0.2 to 20 moles per gram atom of the cobalt makes it possible to separate the reaction product from the reaction mixture by direct distillation without any such special operation for the catalyst separation as required in the conventional processes. The distillation residue which contains the catalyst can be recycled for the reuse thereof in the carbonylation.Type: GrantFiled: July 23, 1979Date of Patent: June 8, 1982Assignee: Kuraray Co. Ltd.Inventors: Mitsuo Matsumoto, Masuhiko Tamura
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Patent number: 4301090Abstract: Oxygenated organic compounds, e.g. esters, aldehydes, and amides, are prepared by reacting an olefinically unsaturated compound with carbon monoxide and a compound containing a replaceable hydrogen atom in the presence of a catalyst comprising cobalt carbonyl and a polyamine promoter ligand. These reactions are carried out under relatively mild conditions of temperature and pressure.Type: GrantFiled: August 13, 1979Date of Patent: November 17, 1981Assignee: Standard Oil CompanyInventors: Frederick A. Pesa, Thomas A. Haase